Abstract
Even in the early days of investigations on penicillin synthesis by direct fermentation, the importance of incorporating different side chains for antibiotic activity was evident. Addition of various mono-substituted acetic acids to the Penicillium fermentation medium gave the corresponding new penicillins with varying activity profiles. Notably, such studies led to phenoxymethyl penicillin (Pen V), which is acid stable and orally active. Up to the late 50′s, only two of the many penicillins produced by fermentation, namely Pen G and Pen V, proved to be clinically useful, though indeed these have stood the test of time. Further progress here was limited, as a result of the selective biochemical incorporation of side-chains by the Penicillium fungus (restricted mainly to aliphatic or aryl aliphatic carboxylic acids).
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§5 Further Reading
5.1 Books
J.H. Sheenan, ‘The Enchanted Ring, The untold story of Penicillin’. MIT Press, Cambridge, Massachusetts; London, England (1982).
E.H. Flynn (ed.), ‘Cephalosporins and Penicillins: chemistry and biology’. Academic Press, New York and London (1972).
J. Baddiley and E.P. Abraham, ‘Penicillin Fifty years after Fleming’. The Royal Society, London (1980).
5.2 Reviews
Reports from Michael Barber and Associates (UK): Chemica 1, Penicillin (1986), Chemica 2, 6-APA, 7-ADCA (1986), Chemica 3, Semisynthetic Penicillins (1987), Useful Book (1991), The Manufacture of Penicillins and its derivatives (1999), The Penicillins Business (1996) and several other MBA publications.
J. Wilson, ‘Antibacterial products and markets’, Scrip Reports, UK (1997).
S.C. Stinson, ‘Drug Firms restock Antibacterial Arsenal’, Chem. & Eng. News, Sept. 1996, 75–100.
C.H. Henry, ‘Antibiotic Resistance’, Chem. & Eng. News, March 2000, 41–58.
M.I. Page and A.P. Laws, ‘The Mechanism of catalysis and the inhibition of β-lactamases’, Chem. Commun. 1998, 1609–1617.
A. Bruggink, E.C. Roos and E. de Vroom, ‘Penicillin Acylase in the Industrial Production of β-lactam Antibiotics’, Organic Process Research & Development, 2, 128–133 (1998).
E.J.A.X. van de Sandt and E. de Vroom, ‘Innovations in cephalosporin and penicillin production: Painting the antibiotics industry green’. Chemica Oggi, May 2000, 72–75.
A. Bruggink, ‘Green solutions for chemical challenges, biocatalysis in the synthesis of semi-synthetic antibiotics’, in B. Zwanenburg et. al. (eds.), Enzymes in Action, 449–458 (2000), Kluwer Academic Publishers (The Netherlands).
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© 2001 Springer Science+Business Media Dordrecht
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Bruggink, A., Roy, P.D. (2001). Industrial Synthesis of Semisynthetic Antibiotics. In: Bruggink, A. (eds) Synthesis of β-Lactam Antibiotics. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-0850-1_1
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